Acetic Acid → HCID 11978048, compound

HRID 2247734Notes

Reaction equation

HRID 2247734 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:28][N:29]2[CH2:32][CH:31]([C:33]([O:35]C)=[O:34])[CH2:30]2)[S:6][C:7]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])=[CH:15][CH:14]=2)[O:10][N:9]=1)[CH3:2].[OH-].[Na+].C(O)(=O)C.C(O)(=O)C(O)=O>O1CCOCC1.CO.O>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:28][N:29]2[CH2:32][CH:31]([C:33]([OH:35])=[O:34])[CH2:30]2)[S:6][C:7]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])=[CH:15][CH:14]=2)[O:10][N:9]=1)[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 971Oxalic AcidHCID 14798Sodium HydroxideHCID 68524254HCID 68524254, compound

Product 1

HCID 11978048HCID 11978048, compoundYield 75.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 1-[(4-ethyl-5-{5-[4-(2-methoxyphenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methyl]azetidine-3-carboxylate (86 mg, 0.17 mmol) that was obtained in Example 21 (21c) in dioxane (3 ml) was added a 1N aqueous solution of sodium hydroxide (0.51 ml, 0.51 mmol) with stirring, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, acetic acid (29 μl, 0.51 mmol) was added to the reaction mixture to quench the reaction, and the resulting mixture was evaporated in vacuo. Subsequently, to the residue obtained were added successively methanol (2 ml) and water (1 ml) with stirring, and furthermore a solution of oxalic acid (8 mg, 0.09 mmol) in methanol (0.5 ml) was added, and then the resulting mixture was stirred for 30 minutes. The white solid precipitated was collected by filtration using a Kiriyama funnel, washed with a mixed solvent of water and methanol (3:7) and dried in vacuo to afford the title compound (63 mg) in a yield of 69% as a white crystalline solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. stirringAfter stirring
  3. customto quench
  4. customthe reaction
  5. customthe resulting mixture was evaporated in vacuo
  6. customSubsequently, to the residue obtained
  7. stirringwith stirring
  8. stirringthe resulting mixture was stirred for 30 minutes
  9. customThe white solid precipitated
  10. filtrationwas collected by filtration
  11. washwashed with a mixed solvent of water and methanol (3:7)
  12. customdried in vacuo

Sources & evidence

ORD record
ord-7488a260992d4af3b1472455dc6a31dc
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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